Copper azodyestuffs



Patented Fee. 22, rear.

barren snares nane mann r castes.

THOMAS H. LEAIVIING, DECEASED, LATE F BUFFALO, NEW YORK; BY BERYL LEAH-ING, ADMINISTRATOR, OF BUFFALO, NEW YORK, ASSIGNOR TO NATIONAL ANILINE &CHEMICAL 00., INCLOE NEW YORK, N. Y., A CORPORATION OF NEW YORK.

corraa .a'zonrnsrurrs.

No Drawing.

This invention relates to the production of new copper compounds ofsubstantive azodyestuffs which are of value for dyeing cotton and silk.The fabrics, or other material, dyed with the new dyestuffs also form apart of the present invention.

It is known that copper compounds of substantive azodyestuffs,hereinafter called cop er azodyestufis, can be produced by treatlng withcopper, or a compound of copper, and azodyestufl? obtained by combiningone or two molecules of diazotized 2-aminobe produced from the abovementioned obtained by coupling in the presence of sodi- 60 um carbonatetwo molecules of diazotized 2- aminobenzoic acid with one molecule of5.5 dihydroxy-ELQ dinapthylamine-7.7--

disulfonic acid are dissolved in about 21,000 parts water at 85 0., and409.5- parts 5 (two molecules) crystallized copper sulfate are slowlyadded to this solution while stirring. The temperature of the mixture ismaintained at about 85 C.,for about one hour and the solution is thenrendered al- 7 kaline by adding to it about 320 arts (eight moles) ofcaustic soda as a 10 percent aqueous solution. The copper dyestufi' isthen salted out at a temperature of about 85 C by the slow addition ofcommon salt 75 to the well stirred solution. About 4500- mixture. andsubsequently salting Application filed J'une 22, 1925. Serial No.38,928.

azodyestufis by subjecting the reaction mixture or product of saidazodyestulfs with copper or copper salts to the action of caustic alkaliin an aqueous medium, andsubsequently isolating the copper azodyestufithus produced.

In carrying out the invention a solution of copper sulfate, or othersoluble cop er salt, is added to a neutral or slightly alka ine aqueoussolution of an azodyestulf obtainable by coupling in {the presence ofsodium carbonate one or two molecules of diazotized Q-aminobenzoic acidor its derivatives or one molecule of a 2-aminobenzoic aci and 'one'molecule of. another diazo compound, with one molecule of 5.5-dihydroxy-2.2 dinaphthylamine 7.7 disulfonic acld and the mixture subsequentlyrendered alkaline, preferably at elevated temperature, by i the additionof caustic alkali and the copper azodyestufi then salted out. andseparated in any suitable manner. i

The following example will further illustrate the invention, but it willbe understood that it is not limited thereto. The parts are by weight.

Ewample.845 parts (one mole) of the dyestufi having the probable formulaand parts of common salt are usually required. The precipitated dyestuifis filtered off,-

pressed and dried.

The dyestuff thus obtained dyes cotton and silk reddish-violet shadeswhich are bri hter than those obtained when .sodium car onate is used asa neutralizing agent. It also has a greater afiinity for vegetable fiberand consequently the dye-baths are more com letely exhausted. In ,thedry and pulverize condition, the newcopper azodyestulf is a dark powdersoluble hiwater with a reddish-violet color and soluble in concentratedsulfuric acid with a brownishred color which on dilution with ice-waterturns blue and finally produces a bluish-red precipitate.

Elil

n l" at ill In the above example, the amount of cop per sulfate employedcan be varied; the use of less amounts than the amount of saturationwith copper tend to produce dyestuffs giving redder shades While the useoi the maximal amounts produce dyestuli's giving hluer shades. Thecopper sulfate can be added, if desired, in the form of an aqueoussolution. The amount of water, of caustic allrali and of salt employedcan also be varied over comparatively wide limits. The host effects areproduced by the use of about two to live molecules of caustic alkali foreach molecule oi copper sulfate employed. S ther ingredients capable ofsupplying copper under the stated conditions may be employed.

lln the ahove enample, the azodyestufl. derived from the two moleculesof dominohenaoie acid and one molecule at hil-dillydrony-EJV-dinaphthylaniinc 7.7" disultonic acid can. be replacedlay an equivalent amount oi other azoclyestutls produced from onemolecule of he latter acid in coinhination with one or two molecules ata diam conipound. one or which is diazotized dominohenaoic acid or aderivative of the same.

lt may he further pointed out that the copper azodycstuttls produced byprocesses wherein sodium carbonate, sodium acetate or other mineral acidbinding agents are employed the neut alizing agents, may upon treatmentwith cuastic soda be subseuucntly converted to the copper dyestufls Oitee present invention.

In the claims it-will he understood that the term Lucid imide represents5.5 dihydrony-QW- dinaphthylamine-i'.""- disultome acid; and that theterm anth'anilic l-aeid imide dyestuii' represents a dyestutl obtainableby combining in an alkaline medium one or two molecular proportions ofdiazotined Q-aminohenzoic acid or its derivatives, or one molecularproportion of diazotized anthranilic acid or derivative and onemolecular proportion of another diazo compound with on molecularproportion of l-acid iinide.

ll claim:

l. A process oat melting a copper azodyestall which comprises treatingan aqueous solution of an anthranilic I-acid iinide dye stullt with acop or salt, then adding sulficient caustic allra i to produce a causticalha rotates line medium and subsequently salting out the copperazodyestuli'.

2. A copper azodyestufl? obtainable by the process as claimed in claim1.

3. A process of making a copper azodycstall which comprises treating anaqueous solution of a (lyestuff produced by combining in the prescenccof sodium carbonate two molecular proportions of diazotized 2-aminobenzoic acid with one molecular pro portion of l-acid imide with asoluable copper salt, subsequently rendering the solution alkaline withcaustic alkali, and then suiting out the copper azodyestutl.

, fir copper aaocilyestufl obtainable by the process as claimed in claim3.

:5. A. process or making a copper azodyestall which comprises treatingwith copper sulfate a solution of the sodium salt at the disaeo dyeproduced by combining two molecular proportions of diazotiaedanthranilic acid with one molecular proportion oi lucid iuiidc, andsubsequently rendering the solu tion strongly alkaline by the additionof caustic soda thereto and then suiting out the copper azodyestull,filtering it oil and dry inp; it.

ti. i l copper azodyestufl' ohtainahle hy the process as claimed inclaim 5.

i. it process or malnnp; a copper aaodyestull' which comprises addingcaustic alkali Bil in excess at elevated temperatures to an aqueoussolution containing the reaction product of a copper salt and ananthranilic lucid imide dyestull, and subsequently saltingr out thecopper aaodyestufil.

it. The process according" to claim 7 in which caustic soda and coppersulfate are respectively the caustic alkali and copper salt employed.

ll. The process according to claim 7, in which caustic soda is thecaustic alkali enrployed. l

10. Material dyed with the copper azodyestuff of claim 93.

11. Material dyed with the copper azodyestud of claim t.

12. Material dyed with the copper azodyestuff of claim 6.

In testimony Whereol I aflix my signature.

ldEltYlh lLEJ il /lllNG, Administrator of Thomas H. looming, de-

concea lot

